40127-91-1

Basic information

• Product Name: 3-amino-6-(chloromethyl)pyrazinecarbonitrile
• Synonyms: 3-amino-6-(chloromethyl)pyrazinecarbonitrile
• CAS NO: 40127-91-1
• Molecular Formula: C₆H₅ClN₄
• Molecular Weight: 168.5837
• EINECS: 254-800-1
• Mol File: 40127-91-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 381.5°C at 760 mmHg
• Flash Point: 184.5°C
• Appearance: /
• Density: 1.44g/cm³
• Vapor Pressure: 5.04E-06mmHg at 25°C
• Refractive Index: 1.599
• PKA: 1.01±0.10(Predicted)
• CAS DataBase Reference: 3-amino-6-(chloromethyl)pyrazinecarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-amino-6-(chloromethyl)pyrazinecarbonitrile(40127-91-1)
• EPA Substance Registry System: 3-amino-6-(chloromethyl)pyrazinecarbonitrile(40127-91-1)

Safety Data

• Hazardous Substances Data: 40127-91-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H5ClN4/c7-1-4-3-10-6(9)5(2-8)11-4/h3H,1H2,(H2,9,10)

Upstream product

• 40127-89-7 3-amino-6-(chloromethyl)-2-pyrazinecarbonitrile 4-oxide 

Downstream Products

• 1053700-95-0 (S)-2-{4-[(5-Amino-6-cyano-pyrazin-2-ylmethyl)-amino]-benzoylamino}-5-tert-butoxycarbonylamino-pentanoic acid tert-butyl ester 
• 64440-74-0 2-amino-3-cyano-5-formylpyrazine 
• 64440-76-2 N-[p-(dimethylamino)phenyl]-α-(2-amino-3-cyano-5-pyrazinyl)nitrone 
• 118869-57-1 N-<4-<<(2-amino-3-cyanopyrazin-5-yl)methyl>amino>benzoyl>-L-glutamic acid 
• 129780-84-3 di-tert-butyl N-<4-<<(4-amino-2-methylpteridin-6-yl)methyl>methylamino>benzoyl>-L-glutamate 
• 129780-82-1 di-tert-butyl N-<4-<<(4-aminopteridin-6-yl)methyl>methylamino>benzoyl>-L-glutamate 
• 129780-80-9 N-<4-<<(4-amino-2-methylpteridin-6-yl)methyl>methylamino>benzoyl>-L-glutamic acid 
• 129780-79-6 N-<4-<<(4-aminopteridin-6-yl)methyl>methylamino>benzoyl>-L-glutamic acid 
• 118869-51-5 N-<4-<<(4-aminopteridin-6-yl)methyl>amino>benzoyl>-L-glutamic acid 
• 129780-83-2 4-<<(4-amino-2-methylpteridin-6-yl)methyl>methylamino>benzoic acid 
• 129780-81-0 4-<<(4-aminopteridin-6-yl)methyl>methylamino>benzoic acid 
• 104438-50-8 2,4-Diamino-6-n-propoxymethylpteridine 
• 104422-65-3 2-Amino-6-ethoxymethyl-4(3H)-pteridinone 
• 40110-13-2 2,4-diamino-6-methoxymethylpteridine 

Relevant articles and documents

Pterin–sulfa conjugates as dihydropteroate synthase inhibitors and antibacterial agents

The sulfonamide class of antibiotics has been in continuous use for over 70?years. They are thought to act by directly inhibiting dihydropteroate synthase (DHPS), and also acting as prodrugs that sequester pterin pools by forming dead end pterin–sulfonamide conjugates. In this study, eight pterin–sulfonamide conjugates were synthesized using a novel synthetic strategy and their biochemical and microbiological properties were investigated. The conjugates were shown to competitively inhibit DHPS, and inhibition was enhanced by the presence of pyrophosphate that is crucial to catalysis and is known to promote an ordering of the DHPS active site. The co-crystal structure of Yersinia pestis DHPS bound to one of the more potent conjugates revealed a mode of binding that is similar to that of the enzymatic product analog pteroic acid. The antimicrobial activities of the pterin–sulfonamide conjugates were measured against Escherichia coli in the presence and absence of folate precursors and dependent metabolites. These results show that the conjugates have appreciable antibacterial activity and act by an on target, anti-folate pathway mechanism rather than as simple dead end products.

Mild and efficient deoxygenation of amine-N-oxides with MoCl5/NaI system

The MoCl5/NaI system was found to be a new reagent for deoxygenation of various amine-N-oxides to the corresponding amines in good to excellent yields under mild conditions. Copyright Taylor & Francis Group, LLC.

Syntheses of labeled vitamers of folic acid to be used as internal standards in stable isotope dilution assays

[2H4]Folic acid was synthesized by deuterating p-aminobenzoic acid, which was then coupled to glutamic acid and 6-formylpterin, Using [2H4]folic acid as starting component enabled the preparation of labeled vitamers tetrahydrofolate, 5-formyltetrahydrofolate, 5-methyltetrahydrofolate, and 10-formylfolate which were characterized by electrospray mass spectrometry and collision-induced dissociation. The mass spectrometric studies confirmed that the compounds could be used as internal standards in stable isotope dilution assays.